Inspired by this year’s music-themed “Christmas School,” today I’m looking at what I consider to be the top five (yes, I know…actually six. I had a Rat Pack tie at the end!), most iconic Christmas songs. When I say iconic, I mean the song and singer together…the type of piece where, when you hear it, you think to yourself “no one else needed to record this song ever, because it’s perfect as it is, and there is no topping it!”

• Bing Crosby–“White Christmas”–No one does Christmas music like Bing, and maybe it’s just because White Christmas is my favorite Christmas movie, but I think this is the song he does best. I’m immediately transported to a different place and time at those opening notes!
• Nat King Cole–“The Christmas Song”–Second only to Bing, Nat also excels at Christmas, and while I especially love his Toys for Tots song, we all know that Nat absolutely owns “Chestnuts Roasting on an Open Fire” (I do also like the rendition they created of him and Natalie Cole singing it together.)
• Andy Williams–“It’s the Most Wonderful Time of the Year”–Another iconic voice at Christmastime, Andy has several songs that he does really well, including “Happy Holidays” and “It’s the Holiday Season,” but “It’s the Most Wonderful Time of the Year” is my favorite, and so recognizable.
• Ella Fitzgerald–“Sleigh Ride”–I don’t know if it’s because it’s been used so well in movies (Elf comes to mind), but “Sleigh Ride” is totally Ella Fitzgerald’s song! This is another example of a song I recognize immediately from just the first few notes, because her version was so distinctive.
• Frank Sinatra–“Christmas Memories”–This is probably the least-known song on the list, and it really captures that sense of nostalgia at Christmastime both in words and music, and Frank sings it with so much emotion, you get the sense he’s really feeling it when he sings “Funny, but comes December, and I remember every Christmas I’ve known.”
• Dean Martin–“I’ve Got My Love to Keep Me Warm”–Between this and “Baby it’s Cold Outside,” Dean is the king of winter songs, but this one is a little less controversial, so I chose it over the other, even though I like both equally well.

What Christmas songs are iconic to you?